P
US7361687B2ExpiredUtilityPatentIndex 95

Arylsulphonamide derivatives and methods of preparing

Assignee: FOURNIER LAB SAPriority: Jun 14, 2002Filed: Jun 12, 2003Granted: Apr 22, 2008
Est. expiryJun 14, 2022(expired)· nominal 20-yr term from priority
Inventors:BARTH MARTINEBONDOUX MICHELDODEY PIERREMASSARDIER CHRISTINELUCCARINI JEAN-MICHEL
A61P 9/12A61P 3/06A61P 37/08A61P 9/10A61P 25/24C07D 239/06A61P 25/00A61P 25/04C07D 233/64A61P 29/00A61P 25/22C07D 409/12
95
PatentIndex Score
62
Cited by
18
References
21
Claims

Abstract

The present invention relates to novel arylsulphonamide compounds, defined by formula I and the description, as well as their method of preparation and their therapeutic use

Claims

exact text as granted — not AI-modified
1. A compound of formula I: 
       
         
           
           
               
               
           
         
         wherein: 
         R 1  is aromatic group, where said aromatic is optionally substituted by one or more atoms or groups of atoms selected from the group consisting of halogen, C 1 -C 3  alkyl, C 1 -C 3  alkoxy, nitro, cyano, trifluoromethyl, and trifluoromethoxy; 
         R 2  is hydrogen or C 1 -C 4  alkyl, where said C 1 -C 4  alkyl is optionally monosubstituted by a phenyl or —CONH 2  or optionally substituted by one or more fluorine atoms; 
         R 3  is hydrogen or hydroxy; 
         R 4  is hydrogen; 
         or R 4 , together with R 3 , forms a —CH═N— or a straight or branched C 2 -C 4  alkylene; 
         R 5  is hydrogen or C 1 -C 3  alkyl; 
         R 6  is hydrogen or halogen; 
         Y is straight or branched saturated C 2 -C 4  alkylene or straight or branched unsaturated C 2 -C 4  alkylene, where said C 2 -C 4  alkylene is optionally interrupted between two carbon atoms by an oxygen atom; 
         or an acid addition salt thereof. 
       
     
     
       2. A compound according to  claim 1 ,
 wherein R 1  is chlorophenyl, dichlorophenyl, trichlorophenyl, chloro-methoxyphenyl, chloro-trifluoromethoxyphenyl, dichloro-trifluoromethyl-phenyl, chlorofluorophenyl, difluorophenyl, trifluoromethyl-phenyl, trifluoromethyl-methoxyphenyl, trifluoromethyl-chlorophenyl trifluoromethoxy-phenyl, tolyl, chlorotolyl, dichlorotolyl, dimethyltolyl, methoxytolyl, methoxy-methyltolyl, dichloromethoxy, trifluoromethoxy-tolyl, naphthyl, nitrophenyl, trifluoromethyl-nitrophenyl, cyanophenyl, or thienyl. 
 
     
     
       3. A compound according to  claim 1 ,
 wherein R 1  is phenyl substituted by one or more atoms or groups of atoms selected from the group consisting of halogen, C 1 -C 3  alkyl, and C 1 -C 3  alkoxy. 
 
     
     
       4. A compound according to  claim 1 ,
 wherein R 2  is C 1 -C 4  alkyl. 
 
     
     
       5. A compound according to  claim 1 ,
 wherein R 2  is hydrogen, methyl, cyclopropyl, trifluoroethyl, isopropyl, —CH 2 CONH, —(CH 2 ) 2 CONH, or phenethyl. 
 
     
     
       6. A compound according to  claim 1 ,
 wherein R 3  is hydrogen. 
 
     
     
       7. A compound according to  claim 1 ,
 wherein R 3  is hydroxy. 
 
     
     
       8. A compound according to  claim 1 ,
 wherein R 4  is hydrogen. 
 
     
     
       9. A compound according to  claim 1 ,
 wherein R 3  and R 4  together form a —N═CH— or C 2 -C 3  alkylene. 
 
     
     
       10. A compound according to  claim 1 ,
 wherein R 3  and R 4  together form —N═CH—, —(CH 2 ) 2 —, or —CH 2 —C(CH 3 ) 2 —. 
 
     
     
       11. A compound according to  claim 1 ,
 wherein R 5  is hydrogen, methyl, ethyl, or isopropyl. 
 
     
     
       12. A compound according to  claim 1 ,
 wherein R 6  is hydrogen, difluoro, or dichloro. 
 
     
     
       13. A compound according to  claim 1 ,
 wherein R 5  and R 6  are hydrogen. 
 
     
     
       14. A compound according to  claim 1 ,
 wherein Y is saturated C 2 -C 4  alkylene or saturated C 2 -C 4  alkylene interrupted by an oxygen atom. 
 
     
     
       15. A compound according to  claim 1 ,
 wherein Y is —(CH 2 ) 2 —, —(CH 2 ) 3 —, —(CH 2 ) 4 —, —CH 2 —CH═CH—, —(CH 2 ) 2 —O—CH 2 —, or 
 
       
         
           
           
               
               
           
         
       
     
     
       16. A compound according to  claim 1 ,
 wherein Y is —(CH 2 ) 4 —. 
 
     
     
       17. A compound according to  claim 1 ,
 wherein Y is —(CH 2 ) 2 —O—CH 2 —. 
 
     
     
       18. A compound according to  claim 1 ,
 wherein said compound is: 
 5-[[(2,4-dichloro-3-methylphenyl)sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-pentanamide; 
 4-[[(2,4-dichloro-3-methylphenyl)sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-butanamide; 
 3-[[(2,4-dichloro-3-methylphenyl)sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-propanamide; 
 4-[[(2,4-dichloro-3-methylphenyl)sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-(2E)-2-butenamide; 
 5-[[(2-chlorophenyl)sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-pentanamide; 
 (2E)-4-[[(2-chlorophenyl)sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-2-butenamide; 
 3-[[(2,3-dichlorophenyl)sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-propanamide; 
 4-[[(2,3-dichlorophenyl)sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-butanamide; 
 5-[[(2,3-dichlorophenyl)sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-pentanamide; 
 (2E)-4-[[(2,3-dichlorophenyl)sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-2-butenamide; 
 5-[[(2,6-dichlorophenyl)sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-pentanamide; 
 (2E)-4-[[(2,6-dichlorophenyl)sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-2-butenamide; 
 5-[methyl[(1-naphthalenyl)sulphonyl]amino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-pentanamide; 
 (2E)-4-[methyl[(1-naphthalenyl)sulphonyl]amino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-2-butenamide; 
 5-[[(2-chlorophenyl)sulphonyl]cyclopropylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-pentanamide; 
 5-[cyclopropyl[(2,3-dichlorophenyl)sulphonyl]amino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-pentanamide; 
 5-[cyclopropyl[(2,6-dichlorophenyl)sulphonyl]amino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-pentanamide; 
 5-[[(2,6-dichlorophenyl)sulphonyl](1-methylethyl)amino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-pentanamide; 
 5-[(2-amino-2-oxoethyl)[(2,4-dichloro-3-methylphenyl)sulphonyl]-amino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-pentanamide; 
 5-[(3-amino-3-oxopropyl)[(2,4-dichloro-3-methylphenyl)sulphonyl]-amino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-pentanamide; 
 3-[[(2,3-dichlorophenyl)sulphonyl](1-methylethyl)amino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-propanamide; 
 3-[[(2,6-dichlorophenyl)sulphonyl](1-methylethyl)amino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-propanamide; 
 2-[2-[[(2-chlorophenyl)sulphonyl]cyclopropylamino]ethoxy]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-acetamide; 
 2-[2-[cyclopropyl[(2,3-dichlorophenyl)sulphonyl]amino]ethoxy]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-acetamide; 
 2-[2-[cyclopropyl[(2,6-dichlorophenyl)sulphonyl]amino]ethoxy]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-acetamide; 
 2-[2-[[(2,4-dichloro-3-methylphenyl)sulphonyl](2-phenylethyl)-amino]ethoxy]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-acetamide; 
 3-[[(2,6-dichlorophenyl)sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-propanamide; 
 3-[cyclopropyl[(2,3-dichlorophenyl)sulphonyl]amino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-propanamide; 
 3-[cyclopropyl[(2,6-dichlorophenyl)sulphonyl]amino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-propanamide; 
 3-[(2,2,2-trifluoroethyl)[(2,3-dichlorophenyl)sulphonyl]amino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-propanamide; 
 3-[(2,2,2-trifluoroethyl)[(2,6-dichlorophenyl)sulphonyl]amino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-propanamide; 
 N-[[4-(4,5-dihydro-1H-imidazol-2yl)phenyl]methyl]-N-methyl-4-[methyl[[2-(trifluoromethyl)phenyl]sulphonyl]amino]-(2E)-2-butenamide; 
 4-[[(2,4-dichloro-3-methylphenyl)sulphonyl]amino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-(2E)-2-butenamide; 
 5-[[(2,4-dichloro-3-methylphenyl)sulphonyl]methylamino]-N-[[4-(5,5-dimethyl-4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-pentanamide; 
 5-[[(2,4-dichloro-3-methylphenyl)sulphonyl]methylamino]-N-[[4-(5,5-dimethyl-4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-pentanamide; 
 2-[2-[[(2,3-dichlorophenyl)sulphonyl]methylamino]ethoxy]-N-methyl-N-[[4-(1,4,5,6-tetrahydro-2-pyrimidinyl)phenyl]methyl]acetamide; 
 2-[2-[[(2,4-dichloro-3-methylphenyl)sulphonyl]methylamino]ethoxy]-N-[[4-(4,5-dihydro-1-methyl-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-acetamide; 
 2-[2-[[(2,3-dichlorophenyl)sulphonyl]methylamino]ethoxy]-N-[[4-(4,5-dihydro-1-methyl-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-acetamide; 
 2-[2-[[(2,4-dichloro-3-methylphenyl)sulphonyl]methylamino]ethoxy]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-acetamide; 
 2-[2-[[(2,3-dichlorophenyl)sulphonyl]methylamino]ethoxy]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-acetamide; 
 2-[2-[[(2,6-dichlorophenyl)sulphonyl]methylamino]ethoxy]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-acetamide; 
 2-[2-[[(2-chlorophenyl)sulphonyl]methylamino]ethoxy]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-acetamide; 
 2-[2-[[(2,3-dichlorophenyl)sulphonyl]methylamino]ethoxy]-N-[[2-fluoro-4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-acetamide; 
 2-[2-[[(2,3-dichlorophenyl)sulphonyl]methylamino]propoxy]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-acetamide; 
 2-[2-[[(2,3-dichlorophenyl)sulphonyl]methylamino]ethoxy]-N-methyl-N-[[4-(1,4,5,6-tetrahydro-2-pyrimidinyl)phenyl]methyl]acetamide; 
 2-[2-[[(2,4-dichloro-3-methylphenyl)sulphonyl]methylamino]ethoxy]-N-[[4-(4,5-dihydro-1-methyl-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-acetamide; 
 2-[2-[[(2,3-dichlorophenyl)sulphonyl]methylamino]ethoxy]-N-[[4-(4,5-dihydro-1-methyl-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-acetamide; 
 N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-2-[2-[methyl[[2-(trifluoromethyl)phenyl]sulphonyl]amino]ethoxy]-acetamide; 
 2-[2-[[(2,4-dichlorophenyl)sulphonyl]methylamino]ethoxy]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-acetamide; 
 2-[2-[[(2,4-dichloro-5-methylphenyl)sulphonyl]methylamino]-ethoxy]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-acetamide; 
 N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-2-[2-[methyl[(2-nitrophenyl)sulphonyl]amino]ethoxy]acetamide; 
 2-[2-[[[2,6-dichloro-4-(trifluoromethyl)phenyl]sulphonyl]-methylamino]ethoxy]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-acetamide; 
 2-[2-[[(2-chloro-3-methylphenyl)sulphonyl]methylamino]ethoxy]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-acetamide; 
 2-[2-[[(2-cyanophenyl)sulphonyl]methylamino]ethoxy]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-acetamide; 
 N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-2-[2-[methyl[(2,3,4-trichlorophenyl)sulphonyl]amino]ethoxy]acetamide; 
 2-[2-[[(3-chloro-2-methylphenyl)sulphonyl]methylamino]ethoxy]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-acetamide; 
 2-[2-[[(2-chloro-4-cyanophenyl)sulphonyl]methylamino]ethoxy]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-acetamide; 
 N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-2-[2-[methyl[[2-nitro-4-(trifluoromethyl)phenyl]sulphonyl]amino]-ethoxy]acetamide; 
 2-[2-[[(2,6-difluorophenyl)sulphonyl]methylamino]ethoxy]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-acetamide; 
 N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-2-[2-[methyl[[4-(trifluoromethoxy)phenyl]sulphonyl]amino]-ethoxy]acetamide; 
 2-[2-[[(2,5-dichlorothien-3-yl)sulphonyl]methylamino]ethoxy]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-acetamide; 
 N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-2-[2-[methyl[(3-methylphenyl)sulphonyl]amino]ethoxy]acetamide; 
 N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-2-[2-[methyl(1-naphthalenylsulphonyl)amino]ethoxy]acetamide; 
 N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-2-[2-[methyl[[3-(trifluoromethyl)phenyl]sulphonyl]amino]-ethoxy]acetamide; 
 2-[2-[[(4-chloro-3-methylphenyl)sulphonyl]methylamino]ethoxy]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-acetamide; 
 2-[2-[[(2,4-difluorophenyl)sulphonyl]methylamino]ethoxy]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-acetamide; 
 2-[2-[[(3-chlorophenyl)sulphonyl]methylamino]ethoxy]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-acetamide; 
 N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-5-[methyl[[2-(trifluoromethyl)phenyl]sulphonyl]amino]pentanamide; 
 5-[[(2,4-dichloro-5-methylphenyl)sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-pentanamide; 
 N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl-N-methyl-5-[methyl[(3-methylphenyl)sulphonyl]amino]pentanamide; 
 N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-5-[[(4-methoxy-2,6-dimethylphenyl)sulphonyl]methylamino]-N-methyl-pentanamide; 
 N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl-N-methyl-5-[methyl[(2,3,4-trichlorophenyl)sulphonyl]amino]pentanamide; 
 N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl-N-methyl-5-[methyl[(2-nitrophenyl)sulphonyl]amino]pentanamide; 
 5-[[(2,4-dichlorophenyl)sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-pentanamide; 
 5-[[(2-chloro-3-methylphenyl)sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-pentanamide; 
 N-[[4-[amino(hydroxyimino)methyl]phenyl]methyl]-5-[[(2,4-dichloro-3-methyl)phenyl]sulphonyl]methylamino]-N-methyl-pentanamide 
 N-[[4-(aminoiminomethyl)phenyl]methyl]-5-[[(2,4-dichloro-3-methylphenyl)sulphonyl]methylamino]-N-methyl-pentanamide; 
 N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-2-[2-[[(4-methoxy-2,6-dimethylphenyl)sulphonyl]methylamino]ethoxy]-N-methyl-acetamide; 
 N-[[4-(4,5-dihydro-1-methyl-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-4-[methyl[[2-(trifluoromethyl)phenyl]sulphonyl]amino]-(2E)-2-butenamide; 
 N-[[4-(4,5-dihydro-1-methyl-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-4-[methyl[[2-(trifluoromethyl)phenyl]sulphonyl]amino]-(2E)-2-butenamide; 
 4-[[(2,3-dichlorophenyl)sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)-2-fluorophenyl]methyl]-N-methyl-(2E)-2-butenamide; 
 4-[[(2-chlorophenyl)sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)-2-fluorophenyl]methyl]-N-methyl-(2E)-2-butenamide; 
 N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-3-[[(4-methoxy-2,6-dimethylphenyl)sulphonyl]methylamino]-N-methyl-propanamide; 
 N-[[2-chloro-4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-5-[[(4-methoxy-2,6-dimethylphenyl)sulphonyl]methylamino]-N-methyl-pentanamide; 
 N-[[2-chloro-4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-5-[[(4-methoxy-2,6-dimethylphenyl)sulphonyl]methylamino]-N-methyl-pentanamide; 
 N-[[4-(4,5-dihydro-1-methyl-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-2-[2-[methyl[[2-(trifluoromethyl)phenyl]sulphonyl]amino]-ethoxy]acetamide; 
 N-[[4-(4,5-dihydro-1-methyl-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-2-[2-[methyl[[2-(trifluoromethyl)phenyl]sulphonyl]amino]-ethoxy]acetamide; 
 N-[[2-chloro-4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-2-[2-[[(2-chlorophenyl)sulphonyl]methylamino]ethoxy]-N-methyl-acetamide; 
 N-[[2-chloro-4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-2-[2-[[(4-methoxy-2,6-dimethylphenyl)sulphonyl]methylamino]ethoxy]-N-methyl-acetamide; 
 N-[[4-(4,5-dihydro-1-(1-methylethyl)-1H-imidazol-2-yl)phenyl]-methyl]-2-[2-[[(4-methoxy-2,6-dimethylphenyl)sulphonyl]methyl-amino]ethoxy]-N-methyl-acetamide; 
 N-[[2-chloro-4-(4,5-dihydro-1-methyl-1H-imidazol-2-yl)phenyl]-methyl]-2-[2-[[(4-methoxy-2,6-dimethylphenyl)sulphonyl]methyl-amino]ethoxy]-N-methyl-acetamide; 
 N-[[2-chloro-4-(4,5-dihydro-1-methyl-1H-imidazol-2-yl)phenyl]-methyl]-2-[2-[[(4-methoxy-2,6-dimethylphenyl)sulphonyl]methyl-amino]ethoxy]-N-methyl-acetamide; 
 N-[[2-chloro-4-(4,5-dihydro-1-methyl-1H-imidazol-2-yl)phenyl]-methyl]-N-methyl-2-[2-[methyl[[2-(trifluoromethyl)phenyl]-sulphonyl]amino]ethoxy]acetamide; 
 N-[[2-chloro-4-(4,5-dihydro-1-methyl-1H-imidazol-2-yl)phenyl]-methyl]-N-methyl-2-[2-[methyl[[2-(trifluoromethyl)phenyl]-sulphonyl]amino]ethoxy]acetamide; 
 2-[2-[[(2-cyanophenyl)sulphonyl]methylamino]ethoxy]-N-[[4-(4,5-dihydro-1-methyl-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-acetamide; 
 2-[2-[[(2-cyanophenyl)sulphonyl]methylamino]ethoxy]-N-[[4-(4,5-dihydro-1-methyl-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-acetamide; 
 2-[2-[[(2-chloro-4-methoxyphenyl)sulphonyl]methylamino]ethoxy]-N-[[4-(4,5-dihydro-1-methyl-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-acetamide; 
 2-[2-[[(2-chloro-4-methoxyphenyl)sulphonyl]methylamino]ethoxy]-N-[[4-(4,5-dihydro-1-methyl-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-acetamide; 
 N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl-N-methyl-3-[methyl[[2-(trifluoromethyl)phenyl]sulphonyl]amino]propanamide; 
 N-[[4-(1-ethyl-4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-2-[2-[methyl[[2-(trifluoromethyl)phenyl]sulphonyl]-amino]ethoxy]acetamide; 
 N-[[4-[1-(1-methylethyl)-4,5-dihydro-1H-imidazol-2-yl]phenyl]-methyl]-N-methyl-2-[2-[methyl[[2-(trifluoromethyl)phenyl]-sulphonyl]amino]ethoxy]acetamide; 
 N-[[4-(1H-1,2,4-triazol-5-yl)phenyl]methyl]-N-methyl-2-[2-[methyl-[(4-methoxy-2,6-dimethylphenyl)sulphonyl]amino]ethoxy]acetamide; 
 (2E)-4-[[(2-chloro-4-fluorophenyl)sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-2-butenamide; 
 (2E)-4-[[[2,6-dichloro-4-(trifluoromethyl)phenyl]sulphonyl]methyl-amino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-2-butenamide; 
 (2E)-4-[[(2,6-difluorophenyl)sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-2-butenamide; 
 (2E)-4-[[(2-nitrophenyl)sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-2-butenamide; 
 (2E)-4-[[(2,4,6-trimethylphenyl)sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-2-butenamide; 
 (2E)-4-[[(2,5-dichlorophenyl)sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-2-butenamide; 
 (2E)-4-[[(2,4-dichlorophenyl)sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-2-butenamide; 
 (2E)-4-[[(3-chloro-2-methylphenyl)sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-2-butenamide; 
 (2E)-4-[[(2-cyanophenyl)sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-2-butenamide; 
 (2E)-4-[[(2-chloro-4-methoxyphenyl)sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-2-butenamide; 
 (2E)-4-[[(2,4-dichloro-5-methylphenyl)sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-2-butenamide; 
 (2E)-4-[[(2,3,4-trichlorophenyl)sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-2-butenamide; 
 (2E)-4-[[[2-chloro-4-(trifluoromethoxy)phenyl]sulphonyl]-methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-2-butenamide; 
 (2E)-4-[[[4-methoxy-2-(trifluoromethyl)phenyl]sulphonyl]methyl-amino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-2-butenamide; 
 (2E)-4-[[(4-methoxy-2,6-dimethylphenyl)sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-2-butenamide; 
 5-[[(2-chloro-4-methoxyphenyl)sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-pentanamide; 
 5-[[(4-methoxy-2-methylphenyl)sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-pentanamide; 
 5-[[[2-methyl-4-(trifluoromethoxy)phenyl]sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-pentanamide; 
 5-[[[4-methoxy-2-(trifluoromethyl)phenyl)sulphonyl]methylamino]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-pentanamide; 
 2-[2-[[(2-chloro-4-methoxyphenyl)sulphonyl]methylamino]ethoxy]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-acetamide; 
 2-[2-[[(4-methoxy-2-methylphenyl)sulphonyl]methylamino]ethoxy]-N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl]-N-methyl-acetamide. 
 or an acid addition salt thereof. 
 
     
     
       19. A compound according to  claim 18 ,
 wherein said acid addition salt is hydrochloride, fumarate, or trifluoroacetate. 
 
     
     
       20. A method for preparing a compound according to  claim 1  or an acid addition salt thereof, comprising the steps consisting of:
 a) reacting an acid of formula II: 
 
       
         
           
           
               
               
           
         
         
           wherein 
           R 1  is aryl, where said aryl is optionally substituted by one or more atoms or groups of atoms selected from the group consisting of halogen, C 1 -C 3  alkyl, C 1 -C 3  alkoxy, nitro, cyano, trifluoromethyl, and trifluoromethoxy; 
           R 2  is hydrogen or C 1 -C 4  alkyl, where said C 1 -C 4  alkyl is optionally monosubstituted by a phenyl or —CONH 2  or optionally substituted by one or more fluorine atoms; 
           Y is straight or branched saturated C 2 -C 4  alkylene or straight or branched unsaturated C 2 -C 4  alkylene, where said C 2 -C 4  alkylene is optionally interrupted between two carbon atoms by an oxygen atom; R 1  is an aromatic system that is non-substituted or substituted by one or more atoms or groups of atoms selected from the group consisting of halogen, C 1 -C 3  alkyl, C 1 -C 3  alkoxy, nitro, cyano, trifluoromethyl and trifluoromethoxy; 
           with an amine of formula III: 
         
       
       
         
           
           
               
               
           
         
         
           wherein 
           R 3  is hydrogen; 
           R 4  is hydrogen; 
           or R 4 , together with R 3 , forms a —CH═N— or a straight or branched C 2 -C 4  alkylene; 
           R′ 5  is hydrogen, C 1 -C 3  alkyl, or an amino-protecting group; 
           R 6  is hydrogen or halogen; 
           wherein the reaction being conducted in a solvent in the presence of at least one activator agent at a temperature of room temperature to 60° C. to obtain the amide of formula: 
         
       
       
         
           
           
               
               
           
         
         
           wherein 
           R 1  is aryl, where said aryl is optionally substituted by one or more atoms or groups of atoms selected from the group consisting of halogen, C 1 -C 3  alkyl, C 1 -C 3  alkoxy, nitro, cyano, trifluoromethyl, and trifluoromethoxy; 
           R 2  is hydrogen or C 1 -C 4  alkyl, where said C 1 -C 4  alkyl is optionally monosubstituted by a phenyl or —CONH 2  or optionally substituted by one or more fluorine atoms; 
           R 3  is hydrogen; 
           R 4  is hydrogen; 
           or R 4 , together with R 3 , forms a —CH═N— or a straight or branched C 2 -C 4  alkylene; 
           R′ 5  is hydrogen, C 1 -C 3  alkyl, or an amino-protecting group; 
           R 6  is hydrogen or halogen; and 
           Y is straight or branched saturated C 2 -C 4  alkylene or straight or branched unsaturated C 2 -C 4  alkylene, where said C 2 -C 4  alkylene is optionally interrupted between two carbon atoms by an oxygen atom; R 1  is an aromatic system that is non-substituted or substituted by one or more atoms or groups of atoms selected from the group consisting of halogen, C 1 -C 3  alkyl, C 1 -C 3  alkoxy, nitro, cyano, trifluoromethyl and trifluoromethoxy; 
         
         b) if necessary, when said R′ 5  is an amino-protecting group, reacting said compound of formula IV to remove said amino-protecting group and replace it by hydrogen, thereby obtaining said compound of formula I, where R 5  is hydrogen; 
         c) if necessary, reacting said compound of formula IV or compound of formula I with a mineral or organic acid to obtain said acid addition salt of said compound of formula IV or said compound of formula I. 
       
     
     
       21. A composition, comprising:
 at least one compound according to  claim 1  or an acid addition salt thereof; and 
 at least one physiologically suitable excipient.

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